Pyridine → Ethyl 1,2,4-thiadiazole-5-carboxylate

Participants

Reaction Conditions

Reaction Steps

To ethyl {[(1E)-(dimethylamino)methylidene]amino}(thioxo)acetate (I78) (1.42 g, 7.54 mmol) and pyridine (1.220 mL, 15.09 mmol) dissolved in Ethanol (20 mL) was added (aminooxy)(hydroxy)sulfane dioxide (0.938 g, 8.30 mmol) dissolved in Ethanol (18 ml) and the mixture stirred at 25° C. for 48 hr. The solvents were concentrated in vacuo and the residue was dissolved in ethyl acetate (50 mL). The solution was washed with saturated sodium bicarbonate solution (25 mL), aqueous phase back extracted with ethyl acetate (25 mL) and the organic extracts were combined. The solution was washed with brine (25 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to afford a crude oil. The crude oil was purified by flash chromatography (Isolera, 50 g, 0-100% ethyl acetate/iso-hexane, 15 column volumes) to afford product in 246 mg.

Provenance & Evidence